SU980628A3 - Способ получени производных андростан-17-она - Google Patents
Способ получени производных андростан-17-она Download PDFInfo
- Publication number
- SU980628A3 SU980628A3 SU772502698A SU2502698A SU980628A3 SU 980628 A3 SU980628 A3 SU 980628A3 SU 772502698 A SU772502698 A SU 772502698A SU 2502698 A SU2502698 A SU 2502698A SU 980628 A3 SU980628 A3 SU 980628A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methoxymethoxy
- cholesten
- hydrogen
- spec
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- YJDYCULVYZDESB-HKQXQEGQSA-N (5r,8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 YJDYCULVYZDESB-HKQXQEGQSA-N 0.000 title 1
- 229930182558 Sterol Natural products 0.000 claims abstract description 5
- 150000003432 sterols Chemical class 0.000 claims abstract description 5
- 235000003702 sterols Nutrition 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 244000005700 microbiome Species 0.000 claims abstract description 4
- 241000186359 Mycobacterium Species 0.000 claims description 11
- -1 methoxymethoxy Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 claims description 5
- 238000011534 incubation Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 claims 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000000855 fermentation Methods 0.000 abstract description 4
- 230000004151 fermentation Effects 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000002328 sterol group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 2
- 235000019838 diammonium phosphate Nutrition 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- XIIAYQZJNBULGD-LUWBJXLVSA-N (5r,8r,9s,10s,13r,14s,17s)-10,13-dimethyl-17-[(2s)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](C)CCCC(C)C)[C@@]2(C)CC1 XIIAYQZJNBULGD-LUWBJXLVSA-N 0.000 description 1
- FYIMAVCIAFVLQP-WQBVUOOHSA-N (8R,9S,10R,13S,14S)-13-(2-hydroxyethoxymethyl)-10-methyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound OCCOC[C@@]12C(CC[C@H]1[C@@H]1CC=C3CCCC[C@]3(C)[C@H]1CC2)=O FYIMAVCIAFVLQP-WQBVUOOHSA-N 0.000 description 1
- NXLVXFUJGPVWAM-HYFVCSRDSA-N (8S,9S,10R,13R,14S,17R)-17-[(2R)-7-(1-ethoxyethoxy)-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C(C)OC(C)OCC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C NXLVXFUJGPVWAM-HYFVCSRDSA-N 0.000 description 1
- YOHUUFNWBNBROB-VQVGGTNESA-N (8S,9S,10R,13R,14S,17R)-17-[(2R)-7-(methoxymethoxy)-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound COCOCC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C YOHUUFNWBNBROB-VQVGGTNESA-N 0.000 description 1
- MNOAOFLIFDRILH-QAGGRKNESA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 MNOAOFLIFDRILH-QAGGRKNESA-N 0.000 description 1
- IOFPEFHYDZRGPP-VQVGGTNESA-N 2-[(6R)-6-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptoxy]ethanol Chemical compound OCCOCC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C IOFPEFHYDZRGPP-VQVGGTNESA-N 0.000 description 1
- NPYXBHZQVNRAOF-KZSQEHGRSA-N 2-[[(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]ethanol Chemical compound C1C=C2CC(OCCO)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 NPYXBHZQVNRAOF-KZSQEHGRSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- CYWWMFJMFFDFHD-UHFFFAOYSA-N Cl.[O-2].[Na+].[Na+] Chemical compound Cl.[O-2].[Na+].[Na+] CYWWMFJMFFDFHD-UHFFFAOYSA-N 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- LYXSZZQTCWJJFR-UHFFFAOYSA-N ethyl acetate;formaldehyde Chemical compound O=C.CCOC(C)=O LYXSZZQTCWJJFR-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/005—Degradation of the lateral chains at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/863—Mycobacterium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762632677 DE2632677A1 (de) | 1976-07-16 | 1976-07-16 | Verfahren zur herstellung von androstan-17-on-derivaten und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU980628A3 true SU980628A3 (ru) | 1982-12-07 |
Family
ID=5983514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772502698A SU980628A3 (ru) | 1976-07-16 | 1977-07-15 | Способ получени производных андростан-17-она |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4179336A (enExample) |
| JP (1) | JPS5315493A (enExample) |
| AT (1) | AT363196B (enExample) |
| BE (1) | BE856860A (enExample) |
| CH (3) | CH627190A5 (enExample) |
| CS (1) | CS200517B2 (enExample) |
| DD (4) | DD132439A5 (enExample) |
| DE (1) | DE2632677A1 (enExample) |
| DK (1) | DK142372C (enExample) |
| FR (4) | FR2365588A1 (enExample) |
| GB (1) | GB1585786A (enExample) |
| HU (4) | HU182790B (enExample) |
| IE (1) | IE45304B1 (enExample) |
| IT (1) | IT1077339B (enExample) |
| NL (1) | NL7706638A (enExample) |
| SE (1) | SE440779B (enExample) |
| SU (1) | SU980628A3 (enExample) |
| YU (1) | YU164277A (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55148083A (en) * | 1979-05-04 | 1980-11-18 | Mitsubishi Chem Ind Ltd | Microorganism |
| JPS55150893A (en) * | 1979-05-11 | 1980-11-25 | Mitsubishi Chem Ind Ltd | Novel microorganism |
| JPS578794A (en) * | 1980-06-17 | 1982-01-18 | Mitsubishi Chem Ind Ltd | Preparation of androstane-type steroid |
| US4755463A (en) * | 1982-05-25 | 1988-07-05 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| US4444884A (en) * | 1982-05-25 | 1984-04-24 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| EP0738703B1 (en) * | 1995-02-28 | 2002-05-22 | Nippon Shokubai Co., Ltd. | Acrylic acid derivatives, method for preparing the acrylic acid derivatives, and acrylic acid polymers |
| MXPA05007628A (es) * | 2003-05-23 | 2005-10-19 | Nektar Therapeutics Al Corp | Derivados de polimeros que tienen arreglos de atomos particulares. |
| JP5701308B2 (ja) * | 2009-10-29 | 2015-04-15 | インダストリー−アカデミック コーポレーション ファウンデーション，ヨンセイ ユニバーシティ | 新規血管漏出遮断剤 |
| WO2012116290A2 (en) | 2011-02-25 | 2012-08-30 | Washington University | Neuroactive 17(20)-z-vinylcyano-substituted steroids, prodrugs thereof, and methods of treatment using same |
| EP3572417B1 (en) | 2011-10-14 | 2025-12-17 | Sage Therapeutics, LLC | 3,3 disubstituted 19-nor pregnane compounds, compositions, and uses thereof |
| KR101993899B1 (ko) | 2012-12-18 | 2019-09-24 | 워싱톤 유니버시티 | 신경활성 19-알콕시-17-치환된 스테로이드, 그의 전구약물, 및 그를 사용한 치료 방법 |
| WO2014127201A1 (en) * | 2013-02-15 | 2014-08-21 | Washington University | Neuroactive enantiomeric 15-, 16- and 17-substituted steroids as modulators for gaba type-a receptors |
| US9512170B2 (en) | 2013-03-01 | 2016-12-06 | Washington University | Neuroactive 13, 17-substituted steroids as modulators for GABA type-A receptors |
| US9365502B2 (en) | 2013-03-11 | 2016-06-14 | Washington University | Neuroactive substituted cyclopenta[b]phenanthrenes as modulators for GABA type-A receptors |
| US9562026B2 (en) | 2013-03-14 | 2017-02-07 | Washington University | Neuroactive substituted cyclopent[a]anthracenes as modulators for GABA type-A receptors |
| US20160068563A1 (en) | 2013-04-17 | 2016-03-10 | Boyd L. Harrison | 19-nor neuroactive steroids and methods of use thereof |
| ES2998982T3 (en) | 2013-04-17 | 2025-02-24 | Sage Therapeutics Inc | 19-nor neuroactive steroids for inducing sedation |
| SG10201802389SA (en) | 2013-04-17 | 2018-04-27 | Sage Therapeutics Inc | 19-nor c3,3-disubstituted c21-n-pyrazolyl steroids and methods of use thereof |
| US9725481B2 (en) | 2013-04-17 | 2017-08-08 | Sage Therapeutics, Inc. | 19-nor C3, 3-disubstituted C21-C-bound heteroaryl steroids and methods of use thereof |
| PL3021852T3 (pl) | 2013-07-19 | 2021-07-05 | Sage Therapeutics, Inc. | Neuroaktywne steroidy, kompozycje i ich zastosowania |
| HUE052308T2 (hu) | 2013-08-23 | 2021-04-28 | Sage Therapeutics Inc | Neuroaktív szteroidok, készítmények és alkalmazásuk |
| WO2015195962A1 (en) | 2014-06-18 | 2015-12-23 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| AR102306A1 (es) | 2014-10-16 | 2017-02-15 | Sage Therapeutics Inc | Esteroides neuroactivos útiles en el tratamiento de enfermedades del snc |
| ME03809B (me) | 2014-10-16 | 2021-04-20 | Sage Therapeutics Inc | KOMPOZICIJE I POSTUPCI ZA LEČENJE POREMEĆAJA CNS-a |
| EP3224269B1 (en) | 2014-11-27 | 2020-02-26 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| EP3250210B1 (en) | 2015-01-26 | 2020-12-02 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| US10329320B2 (en) | 2015-02-20 | 2019-06-25 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| EP3481844B1 (en) | 2016-07-11 | 2024-04-17 | Sage Therapeutics, Inc. | C7, c12, and c16 substituted neuroactive steroids and their methods of use |
| ES2965214T3 (es) | 2016-07-11 | 2024-04-11 | Sage Therapeutics Inc | Esteroides neuroactivos sustituidos en C17, C20 y C21 y sus procedimientos de utilización |
| US11643434B2 (en) | 2019-05-31 | 2023-05-09 | Sage Therapeutics, Inc. | Neuroactive steroids and compositions thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3451892A (en) * | 1965-10-19 | 1969-06-24 | Schering Corp | Process for the preparation of steroidal compounds |
| NL6705450A (enExample) * | 1965-10-22 | 1968-10-21 | ||
| US3684657A (en) * | 1970-05-11 | 1972-08-15 | Searle & Co | Selective microbiological degradation of steroidal 17-alkyls |
| US3759791A (en) * | 1970-12-10 | 1973-09-18 | Searle & Co | Selective microbiological preparation of androst-4-ene-3,17-dione |
| US3738983A (en) * | 1971-08-06 | 1973-06-12 | Searle & Co | Process for the preparation of 3-(3beta,17beta-dihydroxyandrost-5-en-17alpha-yl) propionic acid gamma-lactone |
| DE2534911C2 (de) * | 1975-08-01 | 1985-04-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von 5-Androsten-17-on-Derivaten |
-
1976
- 1976-07-16 DE DE19762632677 patent/DE2632677A1/de active Granted
-
1977
- 1977-06-16 NL NL7706638A patent/NL7706638A/xx not_active Application Discontinuation
- 1977-07-01 YU YU01642/77A patent/YU164277A/xx unknown
- 1977-07-06 US US05/813,391 patent/US4179336A/en not_active Expired - Lifetime
- 1977-07-12 CH CH861377A patent/CH627190A5/de not_active IP Right Cessation
- 1977-07-13 CS CS774682A patent/CS200517B2/cs unknown
- 1977-07-13 AT AT0504677A patent/AT363196B/de not_active IP Right Cessation
- 1977-07-13 IE IE1456/77A patent/IE45304B1/en unknown
- 1977-07-14 DD DD7700200065A patent/DD132439A5/xx not_active IP Right Cessation
- 1977-07-14 DD DD77206210A patent/DD137235A5/xx unknown
- 1977-07-14 DD DD77206205A patent/DD136141A5/xx unknown
- 1977-07-14 SE SE7708192A patent/SE440779B/xx not_active IP Right Cessation
- 1977-07-14 DD DD77206207A patent/DD136142A5/xx unknown
- 1977-07-15 HU HU8019A patent/HU182790B/hu unknown
- 1977-07-15 SU SU772502698A patent/SU980628A3/ru active
- 1977-07-15 HU HU8018A patent/HU182789B/hu unknown
- 1977-07-15 BE BE179384A patent/BE856860A/xx not_active IP Right Cessation
- 1977-07-15 HU HU77SCHE614A patent/HU179344B/hu not_active IP Right Cessation
- 1977-07-15 DK DK323677A patent/DK142372C/da not_active IP Right Cessation
- 1977-07-15 GB GB29800/77A patent/GB1585786A/en not_active Expired
- 1977-07-15 JP JP8493277A patent/JPS5315493A/ja active Granted
- 1977-07-15 IT IT25807/77A patent/IT1077339B/it active
- 1977-07-15 HU HU8020A patent/HU182681B/hu unknown
- 1977-07-18 FR FR7721932A patent/FR2365588A1/fr active Granted
-
1978
- 1978-03-07 FR FR7806456A patent/FR2372174A1/fr active Pending
- 1978-03-07 FR FR7806455A patent/FR2372175A1/fr active Pending
- 1978-03-07 FR FR7806457A patent/FR2372176A1/fr active Pending
-
1981
- 1981-06-23 CH CH415381A patent/CH629503A5/de not_active IP Right Cessation
- 1981-06-23 CH CH415281A patent/CH629222A5/de not_active IP Right Cessation
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